P
US9937200B2ActiveUtilityPatentIndex 83

Skin compositions and methods of use thereof

Assignee: SHISEIDO AMERICAS CORPPriority: Aug 31, 2010Filed: Apr 11, 2016Granted: Apr 10, 2018
Est. expiryAug 31, 2030(~4.2 yrs left)· nominal 20-yr term from priority
Inventors:YU BETTYLOMAKIN JOSEPHKANG SOO-YOUNGADAMS BENJAMIN W
A61P 17/00A61P 17/02A61K 8/345A61Q 19/00A61K 8/0204A61K 2800/95A61K 8/25A61K 8/891A61K 8/895A61L 26/0095A61Q 19/08A61L 26/0019A61Q 1/02A61K 8/894A61K 2800/43A61K 31/765A61K 2800/58A61Q 19/06A61K 2800/884A61Q 1/14A61K 8/585A61Q 1/12A61K 2800/412A61K 2800/5922A61K 8/29A61K 8/19C08L 83/04
83
PatentIndex Score
7
Cited by
135
References
37
Claims

Abstract

Compositions and methods useful for delivering an agent to a subject are described. The methods include applying to the subject's skin a composition comprising a reactive reinforcing component, a cross-linking component, and one or more agents, wherein the cross-linking component catalyzes an in situ reaction on the skin, thereby delivering the agent to the subject.

Claims

exact text as granted — not AI-modified
The invention claimed is: 
     
       1. A method for delivering an agent to a subject, comprising applying to the subject's skin a formulation comprising:
 a) a reactive reinforcing component comprising 
 (i) a reactive constituent comprising at least one alkenyl functionalized organopolysiloxane and at least one hydride functionalized polysiloxane, 
 wherein the at least one alkenyl functionalized organopolysiloxane comprises vinyl groups, 
 (ii) a reinforcing constituent, and 
 (iii) optionally one or more agents; 
 wherein the reactive reinforcing component has a molar ratio of vinyl to hydride functional groups of about 1:10 to about 1:100, and 
 b) a cross-linking component comprising a metal catalyst and optionally one or more agents; 
 wherein after the cross-linking component is contacted with the reactive reinforcing component, a film is formed in situ on the skin, thereby delivering the agent to the subject, and 
 wherein the one or more agents is present in at least a) or b). 
 
     
     
       2. The method of  claim 1 , wherein the agent is a cosmetic or a therapeutic agent. 
     
     
       3. The method of  claim 2 , wherein the cosmetic or therapeutic agent is selected from the group consisting of sunscreens, anti-aging agents, anti-acne agents, anti-wrinkle agents, spot reducers, anti-oxidants, and vitamins. 
     
     
       4. The method of  claim 1 , wherein the at least one alkenyl functionalized organopolysiloxane is a combination of at least one high viscosity organopolysiloxane and at least one low viscosity organopolysiloxane. 
     
     
       5. The method of  claim 4 , wherein the at least one high viscosity organopolysiloxane has a viscosity of about 100,000 to about 500,000 cSt or cP at 25° C., and the at least one low viscosity organopolysiloxane has a viscosity of about 500 to about 50,000 cSt or cP at 25° C. 
     
     
       6. The method of  claim 1 , wherein the reinforcing constituent is selected from the group consisting of optionally surface treated mica, zinc oxide, titanium dioxide, aluminum oxide, clay and silica. 
     
     
       7. The method of  claim 1 , wherein the reactive reinforcing component has a molar ratio of vinyl to hydride functional groups of about 1:15 to about 1:90. 
     
     
       8. The method of  claim 1 , wherein the reactive reinforcing component has a molar ratio of vinyl to hydride functional groups of about 1:25 to about 1:70. 
     
     
       9. The method of  claim 8 , wherein:
 the at least one alkenyl functionalized organopolysiloxane is vinyl terminated polydimethylsiloxane; and 
 the at least one hydride functionalized polysiloxane is methylhydrosiloxane-dimethylsiloxane copolymers, trimethylsiloxy terminated. 
 
     
     
       10. The method of  claim 9 , wherein the cross-linking component further comprises a vinyl terminated organopolysiloxane. 
     
     
       11. The method of  claim 8 , wherein:
 the at least one alkenyl functionalized organopolysiloxane is a polymer of formula IIa and the at least one hydride functionalized polysiloxane is a polymer of formula III: 
 
       
         
           
           
               
               
           
         
       
       and wherein:
 R 1a ′, R 3a ′, R 4a ′, R 5a ′,R 6a ′, R 8a ′, R 9a ′ and R 10a ′ are each independently C 1-20  alkyl, C 2-20  alkenyl, C 5-10  aryl, hydroxyl or C 1-20  alkoxyl; 
 p and q are each independently an integer from between 10 and 6000; 
 R 1b , R 2b , R 3b , R 6b , R 7b  and R 8b  are C 1-20  alkyl; 
 R 4b , R 5b , R 9b , R 10b , R 7b  are each independently selected from the group consisting of hydrogen, C 1-20  alkyl, C 2-20  alkenyl, C 5-10  aryl, hydroxyl and C 1-20  alkoxyl, wherein at least two of R 4b , R 5b , R 9b , R 10b  are hydrogen; and 
 m and n are each independently an integer from between 10 and 6000. 
 
     
     
       12. The method of  claim 8 , wherein:
 the cosmetic or therapeutic agent is selected from the group consisting of sunscreens, anti-aging agents, anti-acne agents, anti-wrinkle agents, spot reducers, anti-oxidants, and vitamins; 
 the reactive reinforcing component comprises a vinyl terminated organopolysiloxane having a viscosity between about 150,000 and about 185,000 cSt or cP at 25° C., and an alkyl terminated hydride functionalized polysiloxane having a viscosity of between about 30 and about 100 cSt or cP at 25° C.; and 
 the cross-linking component comprises a platinum catalyst. 
 
     
     
       13. The method of  claim 1 , wherein the reactive reinforcing component has a molar ratio of vinyl to hydride functional groups of about 1:30 to about 1:60. 
     
     
       14. The method of  claim 13 , wherein:
 the at least one alkenyl functionalized organopolysiloxane is vinyl terminated polydimethylsiloxane; and 
 the at least one hydride functionalized polysiloxane is methylhydrosiloxane- dimethylsiloxane copolymers, trimethylsiloxy terminated. 
 
     
     
       15. The method of  claim 14 , wherein the cross-linking component further comprises a vinyl terminated organopolysiloxane. 
     
     
       16. The method of  claim 13 , wherein:
 the at least one alkenyl functionalized organopolysiloxane is a polymer of formula IIa and the at least one hydride functionalized polysiloxane is a polymer of formula III: 
 
       
         
           
           
               
               
           
         
       
       and wherein:
 R 1a ′, R 3a ′, R 4a ′, R 5a ′, R 6a ′, R 8a ′, R 9a ′ and R 10a ′ are each independently C 1-20  alkyl, C 2-20  alkenyl, C 5-10  aryl, hydroxyl or C 1-20  alkoxyl; 
 p and q are each independently an integer from between 10 and 6000; 
 R 1b , R 2b , R 3b , R 6b , R 7b  and K 8b  are C 1-20  alkyl; 
 R 4b , R 5b , R 9b , R 10b , R 7b  are each independently selected from the group consisting of hydrogen, C 1-20  alkyl, C 2-20  alkenyl, C 5-10  aryl, hydroxyl and C 1-20  alkoxyl, wherein at least two of R 4b , R 5b , R 9b , R 10  are hydrogen; and 
 m and n are each independently an integer from between 10 and 6000. 
 
     
     
       17. The method of  claim 13 , wherein:
 the cosmetic or therapeutic agent is selected from the group consisting of sunscreens, anti- aging agents, anti-acne agents, anti-wrinkle agents, spot reducers, anti-oxidants, and vitamins; 
 the reactive reinforcing component comprises a vinyl terminated organopolysiloxane having a viscosity between about 150,000 and about 185,000 cSt or cP at 25° C., and an alkyl terminated hydride functionalized polysiloxane having a viscosity of between about 30 and about 100 cSt or cP at 25° C.; and 
 the cross-linking component comprises a platinum catalyst. 
 
     
     
       18. The method of  claim 1 , wherein the reactive reinforcing component has a viscosity of about 50,000 to about 700,000 cSt or cP at 25° C. 
     
     
       19. The method of  claim 1 , wherein the at least one hydride functionalized polysiloxane has a viscosity of about 5 to about 11,000 cSt or cP at 25° C. 
     
     
       20. The method of  claim 1 , wherein the at least one alkenyl functionalized organopolysiloxane is vinyl terminated. 
     
     
       21. The method of  claim 1 , wherein the at least one alkenyl functionalized organopolysiloxane is selected from the group consisting of vinyl terminated polydimethylsiloxane; vinyl terminated diphenylsiloxane-dimethylsiloxane copolymers; vinyl terminated polyphenylmethylsiloxane, vinylphenylmethyl terminated vinylphenylsiloxane- phenylmethylsiloxane copolymer; vinyl terminated trifluoropropylmethylsiloxane-dimethylsiloxane copolymer; vinyl terminated diethylsiloxane-dimethylsiloxane copolymer; vinylmethylsiloxane-dimethylsiloxane copolymer, trimethylsiloxy terminated; vinylmethylsiloxane-dimethylsiloxane copolymers, silanol terminated; vinylmethylsiloxane-dimethylsiloxane copolymers, vinyl terminated; vinyl gums; vinylmethylsiloxane homopolymers; vinyl T-structure polymers; monovinyl terminated polydimethylsiloxanes; vinylmethylsiloxane terpolymers; vinylmethoxysilane homopolymers and combinations thereof. 
     
     
       22. The method of  claim 21 , wherein the at least one alkenyl functionalized organopolysiloxane is vinyl terminated polydimethylsiloxane. 
     
     
       23. The method of  claim 1 , wherein the at least one hydride functionalized polysiloxane is selected from the group consisting of hydride terminated polydimethylsiloxane; polyphenyl-(dimethylhydrosiloxy)siloxane, hydride terminated; methylhydrosiloxane-phenylmethylsiloxane copolymer, hydride terminated; methylhydrosiloxane-dimethylsiloxane copolymers, trimethylsiloxy terminated; polymethylhydrosiloxanes, trimethylsiloxy terminated; polyethylhydrosiloxane, triethylsiloxane, methylhydrosiloxane-phenyloctylmethylsiloxane copolymer; methylhydrosiloxane-phenyloctylmethylsiloxane terpolymer and combinations thereof. 
     
     
       24. The method of  claim 23 , wherein the at least one hydride functionalized polysiloxane is methylhydrosiloxane-dimethylsiloxane copolymers, trimethylsiloxy terminated. 
     
     
       25. The method of  claim 1 , wherein the metal catalyst is a platinum catalyst selected from the group consisting of platinum carbonyl cyclovinylmethylsiloxane complexes, platinum divinyltetramethyldisiloxane complexes, platinum cyclovinylmethylsiloxane complexes, platinum octanaldehyde/octanol complexes and combinations thereof. 
     
     
       26. The method of  claim 1 , wherein the film is applied to the skin for at least 1 hour, at least 4 hours, at least 10 hours, at least 16 hours, or at least 24 hours. 
     
     
       27. The method of  claim 1 , wherein the at least one hydride functionalized polysiloxane has a percent SiH content of between about 3 and about 45%; or a SiH content of between about 0.5 and about 10 mmol/g; or a combination of both. 
     
     
       28. The method of  claim 1 , wherein the at least one alkenyl functionalized organopolysiloxane is a polymer of formula IIa and the at least one hydride functionalized polysiloxane is a polymer of formula III: 
       
         
           
           
               
               
           
         
       
       wherein:
 R 1a ′, R 3a ′, R 4a ′, R 5a ′, R 6a ′, R 8a ′, R 9a ′ and R 10a ′ are each independently C 1-20  alkyl, C 2-20  alkenyl, C 5-10  aryl, hydroxyl or C 1-20  alkyl; 
 p and q are each independently an integer from between 10 and 6000; 
 R 1b , R 2b , R 3b , R 6b , R 7b  and R 8b  are C 1-20  alkyl; 
 R 4b , R 5b , R 9b , R 10b , R 7b  are each independently selected from the group consisting of hydrogen, C 1-20  alkyl, C 2-20  alkenyl, C 5-10  aryl, hydroxyl and C 1-20  alkoxyl, wherein at least two of R 4b , R 5b , R 9b , R 10b  are hydrogen; and 
 m and n are each independently an integer from between 10 and 6000. 
 
     
     
       29. The method of  claim 1 , wherein the formulation further comprises one or more feel modifiers, tack modifiers, spreadability enhancers, diluents, adhesion modifiers, optics modifiers, particles, volatile siloxanes, emulsifiers, emollients, surfactants, thickeners, solvents, film formers, humectants, preservatives, or pigments. 
     
     
       30. The method of  claim 1 , wherein:
 the reactive reinforcing component comprises a vinyl terminated organopolysiloxane having a viscosity between about 150,000 and about 185,000 cSt or cP at 25° C., and an alkyl terminated hydride functionalized polysiloxane having a viscosity of between about 30 and about 100 cSt or cP at 25° C.; and 
 the cross-linking component comprises a platinum catalyst. 
 
     
     
       31. The method of  claim 30 , wherein the cross-linking component further comprises a vinyl terminated organopolysiloxane. 
     
     
       32. The method of  claim 30 , wherein:
 the reactive reinforcing component comprises a vinyl terminated polydimethylsiloxane having a viscosity of about 165,000 cSt or cP at 25° C., and an alkyl terminated hydride functionalized polysiloxane having a viscosity of about 45 cSt or cP at 25° C.; and 
 the cross-linking component comprises a platinum divinyltetramethyldisiloxane complex. 
 
     
     
       33. The method of  claim 30 , wherein:
 the reactive reinforcing component comprises a vinyl terminated polydimethylsiloxane having a viscosity of about 165,000 cSt or cP at 25° C., and an alkyl terminated hydride functionalized polysiloxane having a viscosity of about 50 cSt or cP at 25° C.; and 
 the cross-linking component comprises a platinum divinyltetramethyldisiloxane complex. 
 
     
     
       34. The method of  claim 30 , wherein the reactive reinforcing component further comprises a vinyl-terminated polydimethylsiloxane having a viscosity of about 10,000 cSt or cP at 25° C. 
     
     
       35. The method of  claim 1 , wherein the at least one alkenyl functionalized organopolysiloxane comprises at least two vinyl groups. 
     
     
       36. The method of  claim 1 , wherein the film has an appearance of natural skin of the subject. 
     
     
       37. The method of  claim 1 , wherein the subject is a human.

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